Cake Mix Hack: Gluten-Free “Oreo” Surprise Cupcakes with Cookies & Cream Frosting

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I hope everyone had a great Labor Day weekend!  We jumped down to North Carolina for an overnight, to see our friends.  It was great to catch up with all of them and we had breakfast at the Saxapahaw General Store before heading back.  I’ve gushed about my love for this tiny strip of town before, and each year, it gets a little better and a little crunchier–in the best of ways. 😉  Now, in addition to the General Store, the cute industrial apartments, and performing space + Coffee Shop by day/Bar by night venue, Saxapahaw has added a butcher’s shop and a shared-space work studio.  I love this focus on community and local goods!  As for breakfast, M got the usual Coconut-Braised Pork Sandwich (which is still on my list to properly recreate at home!) and I had the brunch special: Eggs Salmon Florentine.  The staff assured me that if was gluten-free, so I was expecting a lighter version of Eggs Benedict Florentine.  You know, some kind of bread, layers of spinach and salmon topped with an egg and their “lemon and caper sauce”.  Instead, in this dish, there wasn’t any bread at all.  The spinach and over-medium eggs were resting on top of a salmon fillet!  It was delicious, and way more protein than I expected.

As for Monday, I had a meeting in the afternoon, so I missed what may have been the highlight of the summer: taking Punc to our community’s “Pool Pawty”.  Each year, the day before they close up the pool, our apartment complex allows the neighborhood to bring their dogs in to swim and play.  Our complex is great at these kind of parties, so M came back with a ton a gift bags full of dog treats, bones, tennis balls, and other swag.  It was pretty awesome!  While she didn’t enjoy the water, Punc did get a doggie massage and a pupcake.  Best of all, she got along with all of the other dogs!

M wasn’t able to take her hiking as often this summer, since it was so hot.  Our area has set a new record for the number of 90+ degree days in July and August.  Ugh.  I am definitely ready for the cooler Fall weather!  So it’s been nice to have this Pool Pawty and playdates with our friends’ dogs to fill in that exercise gap for Punc.  I’m keeping my fingers crossed that this weekend is our last heatwave, so we can start to settle into Fall.  I know M is itching to hike again, as well.

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Today, I am back with another cake mix hack!  They served me so well throughout the summer, being fairly quick and far less fussy than baking a cake from scratch.  I’m still on the search for my “one” cake flour mix.  But, I’m also starting to lean more towards the less sweet pound cake styles.  You know, not quite a quick bread, but not quite a cake.  So maybe I’ll keep my cake mix hacks in my back pocket for occasions that call for frosting and wrappers and all that jazz; and stay content with my simpler options for “everyday” cakes.  These cookies and cream cupcakes have a tasty surprise when you unwrap them: a whole “oreo” cookie at the bottom of each cupcake!  The chocolate cakes are even more fun, because the cake really hides the cookie until you take a bite of the cupcake.

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“Oreo” Surprise Cupcakes with Cookies & Cream Frosting

Serves 12

For the Cupcake

  • 1 box Gluten-free yellow or chocolate cake mix + additional ingredients listed on the back of the package*
  • 2 tsp. vanilla extract
  • 12 (1/2 of a box) “oreo” style gluten-free chocolate wafer, creme-filled cookies**
  • Optional: the filling from 6 additional cookies (save the chocolate cookies for decoration)

For the Frosting

  • 4 oz (half a package) of cream cheese, softened
  • 4 Tbsp (half a stick) of butter, softened
  • 2-3 c. confectioner’s (powdered) sugar
  • 1 tsp. vanilla extract
  • 1 c. crushed “oreo” style cookies (about 10-12 cookies)
  • Optional: 12 individual chocolate cookies leftover from the creme removed for the cupcake batter, for decoration

*I used Aldi’s GFree yellow cake brand, which calls for 3 eggs, 2/3 c. milk, and 1/2 c. oil per box

**I used Trader Joe’s Gluten-Free Jo-Jo cookies

Make the cupcakes

Preheat the oven to the temperature listed on the Cake Mix box.  Fill a cupcake pan with paper cupcake cups and drop one whole “oreo”-style cookie into the bottom of each paper liner.

Remove the inside filling from six cookies, being careful to keep the chocolate wafers intact.  Heat briefly in the microwave to soften, then mix with the liquids called for on the package–if a liquid fat (like oil or melted butter) is called for, this is the best ingredient to mix with the creme filling.  Mix the dry and wet ingredients as instructed on the packaging.  Be sure to include the extra vanilla extract as you mix in the wet ingredient.  Scoop the prepared batter over the cookies in each cup, filling about 3/4 full.  Bake as directed on the packaging.  Allow the cupcakes to cool completely before frosting.

Make the frosting

Leave the cream cheese and butter on the counter as the cupcakes bake and cool, to allow both to soften.  Whip the butter, cream cheese, and vanilla extract on low speed until the mixture is uniform and soft.  Slowly add the confectioner’s sugar, one half-cup at a time, whipping until fully incorporated.  After adding 2 cups of confectioner’s sugar, add in the crushed cookies and mix well.  If the mixture is still soft, continue to add in the additional confectioner’s sugar in 1/2 cup measures.  When the mixing blade or whisk is removed, the frosting should be almost at a stiff peak–the mixture stands straight up from where the whisk was pulled away (if the very tip of the peak falls, that is okay, but the whole peak shouldn’t slump).  Spread or pipe the frosting onto the cupcakes.  Favor a higher pile in the middle, which allows you to sink on of the reserved chocolate wafers upright into the frosting as garnish.

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